pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 17,21-diacetate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 17,21-diacetate
• 英文别名: 17α,21-dihydroxypregna-1,4,9(11)-triene-3,20-dione 17,21-diacetate；17alpha,21-Diacetoxypregna-1,4,9(11)-triene-3,20-dione；[2-[(8S,10S,13S,14S,17R)-17-acetyloxy-10,13-dimethyl-3-oxo-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
• 化学式: C₂₅H₃₀O₆
• 分子量: 426.51
• InChiKey: BNPNBAWUHPQBIR-NTEVEYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  pregna-4,9(11)-diene-17α,21-diol-3,20-dione 17,21-diacetate 在 Nocardioides simplex VKM Ac-2033D 作用下， 以 phosphate buffer 为溶剂， 生成 delta皮质素烯乙酸酯 、 泼尼松杂质D 、 pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 17-acetate 、 pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 17,21-diacetate
  参考文献：
  名称：

  Microbial conversion of pregna-4,9(11)-diene-17α,21-diol-3,20-dione acetates by Nocardioides simplex VKM Ac-2033D

  摘要：

  The conversion of pregna-4,9(l I)-diene-17alpha,21-diol-3,20-dione 21-acetate (I) and 17,21-diacetate (VI) by Nocardioides simplex VKM Ac-2033D was studied. The major metabolites formed from I were identified as pregna-1,4,9(l l)-triene-17alpha,21-diol-3,20-dione21-acetate (11) and pregna-1,4,9(l I)-triene-17alpha,21-diol-3,20-dione (IV). Pregna-4,9(l l)-diene-17alpha,21-diol-3,20-dione (111) and pregna-1,4,9(l 1)-triene-17alpha,20beta,21-triol-3-one (V) were formed in minorities. Biotransformation products formed from VI were pregna-1,4,9(l l)-triene17alpha,21-diol-3,20-dione 17,21-diacetate (VII), pregna-1,4,9(11)-triene-17alpha,21-diol-3,20-dione 21-acetate (11), pregna-1,4,9(11)-triene17alpha,21-diol-3,20-dione (IV), pregna-1,4,9(11)-triene-17alpha,21-diol-3,20-dione 17-acetate (VIII), pregna-1,4,9(11)-triene-17alpha,200,21-triol-3-one (V). The conversion pathways were proposed including 1(2)-dehydrogenation, deacetylation, 20beta-reduction and non-enzymatic migration of acyl group from position 17 to 21. The conditions providing predominant accumulation of pregna-1,4,9(l l)-triene-17alpha,2 I -diol-3,20-dione 21-acetate (11) from I and pregna-1,4,9(l l)-triene-17alpha,2 I -diol-3,20-dione 17-acetate (VIII) from VI in a short-term biotransformation were determined. (C) 2003 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(03)00043-6

文献信息

• US4154748A
  申请人：——

  公开号：US4154748A

  公开（公告）日：1979-05-15
• Microbial conversion of pregna-4,9(11)-diene-17α,21-diol-3,20-dione acetates by Nocardioides simplex VKM Ac-2033D
  作者：Victoria V Fokina、Galina V Sukhodolskaya、Boris P Baskunov、Konstantin F Turchin、Galina S Grinenko、Marina V Donova

  DOI：10.1016/s0039-128x(03)00043-6

  日期：2003.5

  The conversion of pregna-4,9(l I)-diene-17alpha,21-diol-3,20-dione 21-acetate (I) and 17,21-diacetate (VI) by Nocardioides simplex VKM Ac-2033D was studied. The major metabolites formed from I were identified as pregna-1,4,9(l l)-triene-17alpha,21-diol-3,20-dione21-acetate (11) and pregna-1,4,9(l I)-triene-17alpha,21-diol-3,20-dione (IV). Pregna-4,9(l l)-diene-17alpha,21-diol-3,20-dione (111) and pregna-1,4,9(l 1)-triene-17alpha,20beta,21-triol-3-one (V) were formed in minorities. Biotransformation products formed from VI were pregna-1,4,9(l l)-triene17alpha,21-diol-3,20-dione 17,21-diacetate (VII), pregna-1,4,9(11)-triene-17alpha,21-diol-3,20-dione 21-acetate (11), pregna-1,4,9(11)-triene17alpha,21-diol-3,20-dione (IV), pregna-1,4,9(11)-triene-17alpha,21-diol-3,20-dione 17-acetate (VIII), pregna-1,4,9(11)-triene-17alpha,200,21-triol-3-one (V). The conversion pathways were proposed including 1(2)-dehydrogenation, deacetylation, 20beta-reduction and non-enzymatic migration of acyl group from position 17 to 21. The conditions providing predominant accumulation of pregna-1,4,9(l l)-triene-17alpha,2 I -diol-3,20-dione 21-acetate (11) from I and pregna-1,4,9(l l)-triene-17alpha,2 I -diol-3,20-dione 17-acetate (VIII) from VI in a short-term biotransformation were determined. (C) 2003 Elsevier Science Inc. All rights reserved.